#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/71/2217138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2217138
loop_
_publ_author_name
'A. Marx'
'R. Suresh'
'Charles C. Kanakam'
'V. Manivannan'
'Chandhra Sekhar Vasam'
_publ_section_title
;
 8-Methoxy-3-(4-methylbenzylidene)-6-(prop-1-enyl)chroman-4-one
;
_journal_coeditor_code           IS2242
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o27
_journal_page_last               o27
_journal_paper_doi               10.1107/S1600536807060989
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C21 H20 O3'
_chemical_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37
_chemical_name_systematic
;
8-Methoxy-3-(4-methylbenzylidene)-6-(prop-1-enyl)chroman-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8550(5)
_cell_length_b                   11.6264(8)
_cell_length_c                   20.9669(14)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      1.86
_cell_volume                     1658.8(2)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'APEX2 (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17310
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0565P)²+0.331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                2054
_reflns_number_total             2941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            is2242.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2217138
_cod_database_fobs_code          2217138
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.72176(17) 0.14365(10) 0.15211(6) 0.0560(4) Uani d . 1
C C11 0.5481(2) 0.19760(14) 0.13450(8) 0.0431(4) Uani d . 1
O O3 0.45043(19) 0.02250(10) 0.08579(7) 0.0622(4) Uani d . 1
O O2 0.66403(19) 0.48556(10) 0.18481(7) 0.0616(4) Uani d . 1
C C17 0.3351(3) 0.36251(16) 0.12538(8) 0.0484(5) Uani d . 1
H H17 0.3131 0.4391 0.1352 0.058 Uiso calc R 1
C C12 0.5149(2) 0.31169(14) 0.14850(8) 0.0431(4) Uani d . 1
C C14 0.4016(3) 0.13375(14) 0.09710(9) 0.0467(4) Uani d . 1
C C13 0.6739(2) 0.38058(14) 0.18298(8) 0.0439(4) Uani d . 1
C C9 0.8458(2) 0.31532(14) 0.21405(8) 0.0429(4) Uani d . 1
C C15 0.2262(3) 0.18653(16) 0.07531(9) 0.0519(5) Uani d . 1
H H15 0.1286 0.1442 0.0511 0.062 Uiso calc R 1
C C16 0.1906(3) 0.30248(16) 0.08862(9) 0.0498(5) Uani d . 1
C C8 0.9929(2) 0.37410(15) 0.24703(8) 0.0461(4) Uani d . 1
H H8 0.9749 0.4534 0.2468 0.055 Uiso calc R 1
C C19 0.0062(3) 0.36065(18) 0.06302(10) 0.0593(5) Uani d . 1
H H19 -0.0081 0.4355 0.0774 0.071 Uiso calc R 1
C C1 1.1769(2) 0.33551(15) 0.28342(8) 0.0436(4) Uani d . 1
C C20 -0.1372(3) 0.32230(19) 0.02369(10) 0.0652(6) Uani d . 1
H H20 -0.1260 0.2473 0.0092 0.078 Uiso calc R 1
C C10 0.8380(3) 0.18735(15) 0.20825(10) 0.0562(5) Uani d . 1
H H10A 0.9711 0.1588 0.2087 0.067 Uiso calc R 1
H H10B 0.7866 0.1565 0.2458 0.067 Uiso calc R 1
C C2 1.3272(3) 0.41550(16) 0.29596(9) 0.0545(5) Uani d . 1
H H2 1.3065 0.4906 0.2814 0.065 Uiso calc R 1
C C4 1.5439(3) 0.27688(17) 0.35240(9) 0.0506(5) Uani d . 1
C C3 1.5067(3) 0.38657(17) 0.32947(9) 0.0568(5) Uani d . 1
H H3 1.6042 0.4423 0.3366 0.068 Uiso calc R 1
C C6 1.2140(3) 0.22494(16) 0.30760(9) 0.0532(5) Uani d . 1
H H6 1.1164 0.1691 0.3012 0.064 Uiso calc R 1
C C5 1.3935(3) 0.19739(17) 0.34087(10) 0.0575(5) Uani d . 1
H H5 1.4144 0.1227 0.3561 0.069 Uiso calc R 1
C C21 -0.3191(3) 0.3854(2) -0.00093(11) 0.0740(7) Uani d . 1
H H21A -0.3129 0.4622 0.0160 0.111 Uiso calc R 1
H H21B -0.4310 0.3464 0.0122 0.111 Uiso calc R 1
H H21C -0.3309 0.3884 -0.0470 0.111 Uiso calc R 1
C C7 1.7370(3) 0.2454(2) 0.39040(10) 0.0685(6) Uani d . 1
H H7A 1.7215 0.2423 0.4353 0.103 Uiso calc R 1
H H7B 1.8339 0.3022 0.3835 0.103 Uiso calc R 1
H H7C 1.7788 0.1716 0.3766 0.103 Uiso calc R 1
C C18 0.3117(3) -0.04441(18) 0.04568(11) 0.0714(6) Uani d . 1
H H18A 0.1910 -0.0487 0.0645 0.107 Uiso calc R 1
H H18B 0.3629 -0.1205 0.0414 0.107 Uiso calc R 1
H H18C 0.2875 -0.0092 0.0041 0.107 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C11 O1 C10 116.25(14) n
O1 C11 C12 123.15(15) n
O1 C11 C14 116.80(15) n
C12 C11 C14 119.95(15) ?
C14 O3 C18 117.44(14) n
C16 C17 C12 121.75(17) ?
C16 C17 H17 119.1 ?
C12 C17 H17 119.1 ?
C11 C12 C17 119.46(15) ?
C11 C12 C13 119.72(15) ?
C17 C12 C13 120.65(15) ?
O3 C14 C15 125.96(16) n
O3 C14 C11 115.04(15) n
C15 C14 C11 119.00(16) ?
O2 C13 C12 121.22(15) n
O2 C13 C9 122.71(15) n
C12 C13 C9 116.06(14) ?
C8 C9 C13 118.29(15) ?
C8 C9 C10 124.61(15) ?
C13 C9 C10 117.05(14) ?
C14 C15 C16 121.81(16) ?
C14 C15 H15 119.1 ?
C16 C15 H15 119.1 ?
C17 C16 C15 118.03(16) ?
C17 C16 C19 120.01(17) ?
C15 C16 C19 121.95(16) ?
C9 C8 C1 131.33(16) ?
C9 C8 H8 114.3 ?
C1 C8 H8 114.3 ?
C20 C19 C16 129.0(2) ?
C20 C19 H19 115.5 ?
C16 C19 H19 115.5 ?
C2 C1 C6 116.74(16) ?
C2 C1 C8 117.80(16) ?
C6 C1 C8 125.46(15) ?
C19 C20 C21 126.7(2) ?
C19 C20 H20 116.7 ?
C21 C20 H20 116.7 ?
O1 C10 C9 115.55(14) n
O1 C10 H10A 108.4 ?
C9 C10 H10A 108.4 ?
O1 C10 H10B 108.4 ?
C9 C10 H10B 108.4 ?
H10A C10 H10B 107.5 ?
C3 C2 C1 121.84(17) ?
C3 C2 H2 119.1 ?
C1 C2 H2 119.1 ?
C3 C4 C5 117.07(17) ?
C3 C4 C7 121.62(17) ?
C5 C4 C7 121.27(18) ?
C4 C3 C2 121.27(17) ?
C4 C3 H3 119.4 ?
C2 C3 H3 119.4 ?
C5 C6 C1 120.76(17) ?
C5 C6 H6 119.6 ?
C1 C6 H6 119.6 ?
C6 C5 C4 122.31(18) ?
C6 C5 H5 118.8 ?
C4 C5 H5 118.8 ?
C20 C21 H21A 109.5 ?
C20 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C20 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C4 C7 H7A 109.5 ?
C4 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C4 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
O3 C18 H18A 109.5 ?
O3 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O3 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.3567(19) n
O1 C10 1.432(2) n
C11 C12 1.383(2) ?
C11 C14 1.408(2) ?
O3 C14 1.364(2) n
O3 C18 1.422(2) n
O2 C13 1.2232(19) n
C17 C16 1.370(2) ?
C17 C12 1.400(2) ?
C17 H17 0.9300 ?
C12 C13 1.470(2) ?
C14 C15 1.378(2) ?
C13 C9 1.484(2) ?
C9 C8 1.339(2) ?
C9 C10 1.493(2) ?
C15 C16 1.404(3) ?
C15 H15 0.9300 ?
C16 C19 1.476(2) ?
C8 C1 1.464(2) ?
C8 H8 0.9300 ?
C19 C20 1.284(3) ?
C19 H19 0.9300 ?
C1 C2 1.389(2) ?
C1 C6 1.394(2) ?
C20 C21 1.484(3) ?
C20 H20 0.9300 ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C2 C3 1.383(3) ?
C2 H2 0.9300 ?
C4 C3 1.376(3) ?
C4 C5 1.384(3) ?
C4 C7 1.505(2) ?
C3 H3 0.9300 ?
C6 C5 1.377(2) ?
C6 H6 0.9300 ?
C5 H5 0.9300 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8 O2 . 0.93 2.39 2.784(2) 106
C7 H7C O2 2_745 0.96 2.57 3.512(4) 166
C10 H10B O2 2_645 0.97 2.46 3.246(4) 138
C21 H21B Cg 1_455 0.96 2.86 3.722(2) 150
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C10 O1 C11 C12 27.3(2)
C10 O1 C11 C14 -156.35(16)
O1 C11 C12 C17 176.39(16)
C14 C11 C12 C17 0.2(3)
O1 C11 C12 C13 1.2(3)
C14 C11 C12 C13 -174.98(16)
C16 C17 C12 C11 -0.6(3)
C16 C17 C12 C13 174.58(17)
C18 O3 C14 C15 2.8(3)
C18 O3 C14 C11 -177.03(17)
O1 C11 C14 O3 3.0(2)
C12 C11 C14 O3 179.47(16)
O1 C11 C14 C15 -176.79(16)
C12 C11 C14 C15 -0.4(3)
C11 C12 C13 O2 165.08(18)
C17 C12 C13 O2 -10.0(3)
C11 C12 C13 C9 -14.0(2)
C17 C12 C13 C9 170.86(16)
O2 C13 C9 C8 2.1(3)
C12 C13 C9 C8 -178.81(16)
O2 C13 C9 C10 179.76(18)
C12 C13 C9 C10 -1.2(2)
O3 C14 C15 C16 -178.93(18)
C11 C14 C15 C16 0.9(3)
C12 C17 C16 C15 1.0(3)
C12 C17 C16 C19 -177.52(17)
C14 C15 C16 C17 -1.2(3)
C14 C15 C16 C19 177.31(18)
C13 C9 C8 C1 178.65(17)
C10 C9 C8 C1 1.2(3)
C17 C16 C19 C20 173.4(2)
C15 C16 C19 C20 -5.1(3)
C9 C8 C1 C2 160.54(19)
C9 C8 C1 C6 -20.4(3)
C16 C19 C20 C21 -179.4(2)
C11 O1 C10 C9 -41.3(2)
C8 C9 C10 O1 -154.41(17)
C13 C9 C10 O1 28.1(2)
C6 C1 C2 C3 1.5(3)
C8 C1 C2 C3 -179.40(17)
C5 C4 C3 C2 -0.5(3)
C7 C4 C3 C2 -178.38(18)
C1 C2 C3 C4 -0.5(3)
C2 C1 C6 C5 -1.5(3)
C8 C1 C6 C5 179.48(18)
C1 C6 C5 C4 0.5(3)
C3 C4 C5 C6 0.5(3)
C7 C4 C5 C6 178.39(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655416
